AU2008249750B2 - Amino-heterocyclic compounds - Google Patents
Amino-heterocyclic compounds Download PDFInfo
- Publication number
- AU2008249750B2 AU2008249750B2 AU2008249750A AU2008249750A AU2008249750B2 AU 2008249750 B2 AU2008249750 B2 AU 2008249750B2 AU 2008249750 A AU2008249750 A AU 2008249750A AU 2008249750 A AU2008249750 A AU 2008249750A AU 2008249750 B2 AU2008249750 B2 AU 2008249750B2
- Authority
- AU
- Australia
- Prior art keywords
- pyrazolo
- methyl
- dihydro
- pyrimidin
- pyrrolidin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 239
- 150000003839 salts Chemical class 0.000 claims abstract description 52
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 13
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
- 101100407341 Drosophila melanogaster Pde9 gene Proteins 0.000 claims abstract 4
- -1 cyano, phenyl Chemical group 0.000 claims description 156
- 238000000034 method Methods 0.000 claims description 151
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 71
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims description 50
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 40
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
- 241000124008 Mammalia Species 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 34
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 33
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 30
- OFCNXPDARWKPPY-UHFFFAOYSA-N allopurinol Chemical compound OC1=NC=NC2=C1C=NN2 OFCNXPDARWKPPY-UHFFFAOYSA-N 0.000 claims description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000003085 diluting agent Substances 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 230000004770 neurodegeneration Effects 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
- 230000007278 cognition impairment Effects 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 230000001737 promoting effect Effects 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- IWWCRDYUDNNLCO-UHFFFAOYSA-N 1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound O1CCC(CC1)N1N=CC2=C1N=CNC2=O IWWCRDYUDNNLCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- JDVREKNHJZBYEO-UHFFFAOYSA-N 1-cyclopentyl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC=NC=2N1C1CCCC1 JDVREKNHJZBYEO-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- XSVMFMHYUFZWBK-NSHDSACASA-N Rivastigmine Chemical compound CCN(C)C(=O)OC1=CC=CC([C@H](C)N(C)C)=C1 XSVMFMHYUFZWBK-NSHDSACASA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000928 benzodioxinyl group Chemical group O1C(=COC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 3
- STXRQVNFUFZKSJ-DNVCBOLYSA-N chembl572747 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CC=CC=C1 STXRQVNFUFZKSJ-DNVCBOLYSA-N 0.000 claims description 3
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000005433 dihydrobenzodioxinyl group Chemical group O1C(COC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims description 3
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims description 3
- 230000006872 improvement Effects 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 229960004640 memantine Drugs 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 229960001685 tacrine Drugs 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- GASDKPVJCSBXQB-SJLPKXTDSA-N 6-[(3S,4S)-1-benzyl-4-ethylpyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C(C)C)CC)N1CC1=CC=CC=C1 GASDKPVJCSBXQB-SJLPKXTDSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 229960003530 donepezil Drugs 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 229960004136 rivastigmine Drugs 0.000 claims description 2
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- JYKMFUMGSVKAKI-DNVCBOLYSA-N 6-[(3S,4S)-4-methyl-1-(quinolin-3-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC=CC2=CC(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CN=C21 JYKMFUMGSVKAKI-DNVCBOLYSA-N 0.000 claims 2
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- NLUPGGKMPPBLIC-RDTXWAMCSA-N 1-cyclopentyl-6-[(3S,4S)-1-[[2-(dimethylamino)pyrimidin-4-yl]methyl]-4-methylpyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CC=NC(N(C)C)=N1 NLUPGGKMPPBLIC-RDTXWAMCSA-N 0.000 claims 1
- IEAYERCWSQIPRD-CRAIPNDOSA-N 1-cyclopentyl-6-[(3S,4S)-4-methyl-1-[(1-methylbenzimidazol-2-yl)methyl]pyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4N(C5=CC=CC=C5N=4)C)C[C@H]3C)=NC=2N1C1CCCC1 IEAYERCWSQIPRD-CRAIPNDOSA-N 0.000 claims 1
- CBGWGZGLFRSMHQ-FZKQIMNGSA-N 1-cyclopentyl-6-[(3S,4S)-4-methyl-1-[(2-methylpyrimidin-4-yl)methyl]pyrrolidin-3-yl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CC=NC(C)=N1 CBGWGZGLFRSMHQ-FZKQIMNGSA-N 0.000 claims 1
- XEJPARKQHKXBCG-IIBYNOLFSA-N 2-[[(3S,4S)-3-ethyl-4-[1-(oxan-4-yl)-4-oxo-5H-pyrazolo[3,4-d]pyrimidin-6-yl]pyrrolidin-1-yl]methyl]benzonitrile Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=CC=C1C#N XEJPARKQHKXBCG-IIBYNOLFSA-N 0.000 claims 1
- KPBYJLQSWDRHOS-DNVCBOLYSA-N 6-[(3S,4S)-1-[(2-methoxyphenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC=C1CN1C[C@@H](C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)[C@H](C)C1 KPBYJLQSWDRHOS-DNVCBOLYSA-N 0.000 claims 1
- DIWYKXFHEOYCND-FOIQADDNSA-N 6-[(3S,4S)-1-[(3-methoxyphenyl)methyl]-4-methylpyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound COC1=CC=CC(CN2C[C@H]([C@H](C)C2)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)=C1 DIWYKXFHEOYCND-FOIQADDNSA-N 0.000 claims 1
- PJEOWYGQYLUFJR-DNVCBOLYSA-N 6-[(3S,4S)-1-benzyl-4-methylpyrrolidin-3-yl]-1-(thian-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCSCC2)C)N1CC1=CC=CC=C1 PJEOWYGQYLUFJR-DNVCBOLYSA-N 0.000 claims 1
- HVNWRVFQXJXFHM-DNVCBOLYSA-N 6-[(3S,4S)-4-ethyl-1-(pyridin-2-ylmethyl)pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=CC=N1 HVNWRVFQXJXFHM-DNVCBOLYSA-N 0.000 claims 1
- XQZJOMSMPDUGCE-DNVCBOLYSA-N 6-[(3S,4S)-4-ethyl-1-[(5-methylpyrazin-2-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CN=C(C)C=N1 XQZJOMSMPDUGCE-DNVCBOLYSA-N 0.000 claims 1
- RVXPQIRDRIYNDK-VQIMIIECSA-N 6-[(3S,4S)-4-ethyl-1-[(6-methoxypyridin-3-yl)methyl]pyrrolidin-3-yl]-1-(oxan-4-yl)-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)CC)N1CC1=CC=C(OC)N=C1 RVXPQIRDRIYNDK-VQIMIIECSA-N 0.000 claims 1
- BORPFOUKOGKLRD-RHSMWYFYSA-N 6-[(3S,4S)-4-methyl-1-(1,5-naphthyridin-4-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CN=C2C(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=NC2=C1 BORPFOUKOGKLRD-RHSMWYFYSA-N 0.000 claims 1
- PAOXLSJYEIANQB-RDTXWAMCSA-N 6-[(3S,4S)-4-methyl-1-(1,8-naphthyridin-4-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC=C2C(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=NC2=N1 PAOXLSJYEIANQB-RDTXWAMCSA-N 0.000 claims 1
- RNKURPCGQFLEQJ-CZUORRHYSA-N 6-[(3S,4S)-4-methyl-1-(pyrido[2,3-b]pyrazin-8-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CN=C2C(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=NC2=N1 RNKURPCGQFLEQJ-CZUORRHYSA-N 0.000 claims 1
- ZAOLCNVFLBSPTP-RHSMWYFYSA-N 6-[(3S,4S)-4-methyl-1-(quinoxalin-6-ylmethyl)pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound N1=CC=NC2=CC(CN3C[C@H]([C@@H](C3)C)C3=NC4=C(C(N3)=O)C=NN4C(C)C)=CC=C21 ZAOLCNVFLBSPTP-RHSMWYFYSA-N 0.000 claims 1
- VMSUDAYERLIVLB-MLGOLLRUSA-N 6-[(3S,4S)-4-methyl-1-[(5-methylpyrazin-2-yl)methyl]pyrrolidin-3-yl]-1-propan-2-yl-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C([C@H]([C@@H](C1)C)C2=NC3=C(C(N2)=O)C=NN3C(C)C)N1CC1=CN=C(C)C=N1 VMSUDAYERLIVLB-MLGOLLRUSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- RHYNVXDLIQWYAD-FOIQADDNSA-N chembl2179100 Chemical compound C1=CC(OC)=CC=C1CN1C[C@@H](C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)[C@H](C)C1 RHYNVXDLIQWYAD-FOIQADDNSA-N 0.000 claims 1
- IWXUVYOOUMLUTQ-CZUORRHYSA-N chembl2179105 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=NC=CC=N1 IWXUVYOOUMLUTQ-CZUORRHYSA-N 0.000 claims 1
- GXVMSDLIIROULV-FZKQIMNGSA-N chembl575790 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CN=C(C)C=N1 GXVMSDLIIROULV-FZKQIMNGSA-N 0.000 claims 1
- LLIYAZFYRUESNK-FZKQIMNGSA-N chembl575791 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCCC2)C)N1CC1=CC(C)=NN1C LLIYAZFYRUESNK-FZKQIMNGSA-N 0.000 claims 1
- SNCRCEGCQVMUBS-DNVCBOLYSA-N chembl583914 Chemical compound N1=CC=2C(=O)NC([C@@H]3CN(CC=4C=C5N=CC=NC5=CC=4)C[C@H]3C)=NC=2N1C1CCCC1 SNCRCEGCQVMUBS-DNVCBOLYSA-N 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 abstract description 5
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- 230000000626 neurodegenerative effect Effects 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 155
- 238000002360 preparation method Methods 0.000 description 131
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000011541 reaction mixture Substances 0.000 description 40
- 239000000243 solution Substances 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 101150041968 CDC13 gene Proteins 0.000 description 24
- 101001117256 Drosophila melanogaster High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A Proteins 0.000 description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- XRPDDDRNQJNHLQ-UHFFFAOYSA-N 2-ethyl-1h-pyrrole Chemical compound CCC1=CC=CN1 XRPDDDRNQJNHLQ-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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| US91733307P | 2007-05-11 | 2007-05-11 | |
| US60/917,333 | 2007-05-11 | ||
| PCT/IB2008/001125 WO2008139293A1 (en) | 2007-05-11 | 2008-05-05 | Amino-heterocyclic compounds |
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| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| US8648085B2 (en) | 2007-11-30 | 2014-02-11 | Boehringer Ingelheim International Gmbh | 1, 5-dihydro-pyrazolo (3, 4-D) pyrimidin-4-one derivatives and their use as PDE9A mudulators for the treatment of CNS disorders |
| UA105362C2 (xx) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | Похідні 1-гетероцикліл-1,5-дигідропіразоло$3,4-d]піримідин-4-ону та їх застосування як модулятори pde9a$производные 1-гетероциклил-1,5-дигидропиразоло$3,4-d] пиримидин-4-она и их применение в качестве модуляторов pde9a |
| PE20110383A1 (es) | 2008-09-08 | 2011-07-15 | Boehringer Ingelheim Int | Pirazolopirimidinonas como inhibidores de la fosfodiesterasa 9a (pde9a) |
| TR201807944T4 (tr) | 2008-11-19 | 2018-06-21 | Forum Pharmaceuticals Inc | (R)-7-kloro-N-(kinüklidin-3-il)benzo[b]tiyofen-2-karboksamit ve bunun farmasötik olarak kabul edilebilir tuzları ile şizofreninin negatif belirtilerinin tedavisi. |
| TWI404721B (zh) * | 2009-01-26 | 2013-08-11 | Pfizer | 胺基－雜環化合物 |
| JP5542196B2 (ja) | 2009-03-31 | 2014-07-09 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １−複素環−１，５−ジヒドロ−ピラゾロ［３，４−ｄ］ピリミジン−４−オン誘導体及びｐｄｅ９ａモジュレーターとしてのそれらの使用 |
| JP5808319B2 (ja) * | 2009-05-11 | 2015-11-10 | フォルム ファーマシューティカルズ、インコーポレイテッド | アセチルコリンエステラーゼ阻害剤と組み合わせた特定のα７ニコチン酸受容体を用いた認知障害の治療 |
| US9468637B2 (en) | 2009-05-13 | 2016-10-18 | Intra-Cellular Therapies, Inc. | Organic compounds |
| JP2013507360A (ja) * | 2009-10-08 | 2013-03-04 | イントラ−セルラー・セラピーズ・インコーポレイテッド | ホスホジエステラーゼ１−標的トレーサーおよび方法 |
| ES2746850T3 (es) | 2010-05-17 | 2020-03-09 | Forum Pharmaceuticals Inc | Formulaciones farmacéuticas que comprenden formas cristalinas de clorhidrato de (R)-7-cloro-N-(quinuclidin-3-il)benzo(b)tiofeno-2-carboxamida monohidratado |
| PL2603511T3 (pl) | 2010-08-12 | 2017-08-31 | Boehringer Ingelheim Int | Pochodne 6-cykloalkilo-1,5-dihydropirazolo[3,4-d]pirymidyn-4-onu i ich zastosowanie jako inhibitorów PDE9A |
| ES2583528T3 (es) | 2010-09-07 | 2016-09-21 | Astellas Pharma Inc. | Compuesto de pirazoloquinolina |
| CN103313988B (zh) * | 2010-09-20 | 2016-06-08 | 论坛医药有限公司 | 咪唑并三嗪酮化合物 |
| US20130040971A1 (en) * | 2011-02-14 | 2013-02-14 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of cns disorders |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| PL2769980T3 (pl) | 2011-10-07 | 2016-07-29 | Eisai R&D Man Co Ltd | Pochodna pirazolochinoliny jako inhibitory PDE9 |
| JP2015531401A (ja) * | 2011-10-10 | 2015-11-02 | ハー・ルンドベック・アクチエゼルスカベット | イミダゾピラジノン骨格を有するｐｄｅ９ｉ |
| US9434733B2 (en) * | 2012-01-26 | 2016-09-06 | H. Lundbeck A/S | PDE9 inhibitors with imidazo triazinone backbone |
| WO2013142269A1 (en) * | 2012-03-19 | 2013-09-26 | Envivo Pharmaceuticals, Inc. | Imidazotriazinone compounds |
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